Incredible sailboat rentals in Massachusetts, United States.

Sailing Reviews in Massachusetts

1. JS

   Jonathan

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.

2. AD

   Alice

   Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

   Captain Lu is THE MAN ! We had an amazing time with him, he’s very nice and extremely knowledgeable. He adjusted the course of the cruise to an easier swell when our friend that is easily seasick started to feel dizzy, and she felt great the entire time! I can only recommend cruising with Captain Lu and will surely be back again !

3. CL

   Cong

   Elegant 43ft Catamaran: Experience Boston Harbor in Style!

   I had a fantastic evening on this beautiful catamaran with a successful proposal to my now fiancee with sunset. Alex was so professional and accommodating, which led to the success. He was fast to respond, accommodating my date change request due to the weather forecast change even though it was within five days. Alex also coordinated well with my photographer, allowing him to board early before picking us up, which kept the proposal a surprise.

4. 

   Mike

   Elegant 43ft Catamaran: Experience Boston Harbor in Style!

   Perfect way to spend a day in Boston Harbor. The crew was so incredible and took amazing care of us. They had everything we would need, including snacks and towels (we usually bring our own, but totally didn't need to!). Would 100% recommend for a relaxing time on the water!

5. cC

   chris

   43' Sailboat, Bristol RI & Beyond

   This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

6. BA

   Bridget

   Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

   Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!